Recognition of N-Alkyl and N-Aryl Acetamides by N-Alkyl Ammonium Resorcinarene Chlorides

Research output: Contribution to journalArticle

Standard

Recognition of N-Alkyl and N-Aryl Acetamides by N-Alkyl Ammonium Resorcinarene Chlorides. / Beyeh, Ngong Kodiah; Ala-Korpi, Altti; Cetina, Mario; Valkonen, Arto; Rissanen, Kari.

In: CHEMISTRY: A EUROPEAN JOURNAL, Vol. 20, No. 46, 10.11.2014, p. 15144–15150.

Research output: Contribution to journalArticle

Harvard

Beyeh, NK, Ala-Korpi, A, Cetina, M, Valkonen, A & Rissanen, K 2014, 'Recognition of N-Alkyl and N-Aryl Acetamides by N-Alkyl Ammonium Resorcinarene Chlorides', CHEMISTRY: A EUROPEAN JOURNAL, vol. 20, no. 46, pp. 15144–15150. https://doi.org/10.1002/chem.201402533

APA

Beyeh, N. K., Ala-Korpi, A., Cetina, M., Valkonen, A., & Rissanen, K. (2014). Recognition of N-Alkyl and N-Aryl Acetamides by N-Alkyl Ammonium Resorcinarene Chlorides. CHEMISTRY: A EUROPEAN JOURNAL, 20(46), 15144–15150. https://doi.org/10.1002/chem.201402533

Vancouver

Author

Beyeh, Ngong Kodiah ; Ala-Korpi, Altti ; Cetina, Mario ; Valkonen, Arto ; Rissanen, Kari. / Recognition of N-Alkyl and N-Aryl Acetamides by N-Alkyl Ammonium Resorcinarene Chlorides. In: CHEMISTRY: A EUROPEAN JOURNAL. 2014 ; Vol. 20, No. 46. pp. 15144–15150.

Bibtex - Download

@article{c7dff9a2a2a8472f812d4847392c01f2,
title = "Recognition of N-Alkyl and N-Aryl Acetamides by N-Alkyl Ammonium Resorcinarene Chlorides",
abstract = "N-Alkyl ammonium resorcinarene chlorides are stabilized by an intricate array of intra- and intermolecular hydrogen bonds that leads to cavitand-like structures. Depending on the upper-rim substituents, self-inclusion was observed in solution and in the solid state. The self-inclusion can be disrupted at higher temperatures, whereas in the presence of small guests the self-included dimers spontaneously reorganize to 1:1 host–guest complexes. These host compounds show an interesting ability to bind a series of N-alkyl acetamide guests through intermolecular hydrogen bonds involving the carbonyl oxygen (C[DOUBLE BOND]O) atoms and the amide (NH) groups of the guests, the chloride anions (Cl−) and ammonium (NH2+) cations of the hosts, and also through CH⋅⋅⋅π interactions between the hosts and guests. The self-included and host–guest complexes were studied by single-crystal X-ray diffraction, NMR titration, and mass spectrometry.",
author = "Beyeh, {Ngong Kodiah} and Altti Ala-Korpi and Mario Cetina and Arto Valkonen and Kari Rissanen",
year = "2014",
month = "11",
day = "10",
doi = "10.1002/chem.201402533",
language = "English",
volume = "20",
pages = "15144–15150",
journal = "CHEMISTRY: A EUROPEAN JOURNAL",
issn = "0947-6539",
number = "46",

}

RIS - Download

TY - JOUR

T1 - Recognition of N-Alkyl and N-Aryl Acetamides by N-Alkyl Ammonium Resorcinarene Chlorides

AU - Beyeh, Ngong Kodiah

AU - Ala-Korpi, Altti

AU - Cetina, Mario

AU - Valkonen, Arto

AU - Rissanen, Kari

PY - 2014/11/10

Y1 - 2014/11/10

N2 - N-Alkyl ammonium resorcinarene chlorides are stabilized by an intricate array of intra- and intermolecular hydrogen bonds that leads to cavitand-like structures. Depending on the upper-rim substituents, self-inclusion was observed in solution and in the solid state. The self-inclusion can be disrupted at higher temperatures, whereas in the presence of small guests the self-included dimers spontaneously reorganize to 1:1 host–guest complexes. These host compounds show an interesting ability to bind a series of N-alkyl acetamide guests through intermolecular hydrogen bonds involving the carbonyl oxygen (C[DOUBLE BOND]O) atoms and the amide (NH) groups of the guests, the chloride anions (Cl−) and ammonium (NH2+) cations of the hosts, and also through CH⋅⋅⋅π interactions between the hosts and guests. The self-included and host–guest complexes were studied by single-crystal X-ray diffraction, NMR titration, and mass spectrometry.

AB - N-Alkyl ammonium resorcinarene chlorides are stabilized by an intricate array of intra- and intermolecular hydrogen bonds that leads to cavitand-like structures. Depending on the upper-rim substituents, self-inclusion was observed in solution and in the solid state. The self-inclusion can be disrupted at higher temperatures, whereas in the presence of small guests the self-included dimers spontaneously reorganize to 1:1 host–guest complexes. These host compounds show an interesting ability to bind a series of N-alkyl acetamide guests through intermolecular hydrogen bonds involving the carbonyl oxygen (C[DOUBLE BOND]O) atoms and the amide (NH) groups of the guests, the chloride anions (Cl−) and ammonium (NH2+) cations of the hosts, and also through CH⋅⋅⋅π interactions between the hosts and guests. The self-included and host–guest complexes were studied by single-crystal X-ray diffraction, NMR titration, and mass spectrometry.

U2 - 10.1002/chem.201402533

DO - 10.1002/chem.201402533

M3 - Article

VL - 20

SP - 15144

EP - 15150

JO - CHEMISTRY: A EUROPEAN JOURNAL

JF - CHEMISTRY: A EUROPEAN JOURNAL

SN - 0947-6539

IS - 46

ER -

ID: 11467736